Stephen Bear Relationships: A Complete Timeline

Few reality TV stars have traced an arc quite like Stephen Bear — from Celebrity Big Brother winner to convicted sex offender and aspiring professional boxer. His relationships with a string of well-known women have played out in public, culminating in a criminal case that sent him to prison.

Full name: Stephen Henry Bear ·
Born: 15 January 1990 ·
Occupation: Former television personality ·
Known for: Winning Celebrity Big Brother 18 ·
Criminal conviction: Voyeurism and disclosing private sexual photographs (2023) ·
Boxing ambition: Aims to become first reality star to turn professional and win undisputed heavyweight title

Seven key facts that frame Stephen Bear’s public profile — from his birth in Essex to his criminal record:

The implication: Bear’s trajectory from reality TV winner to convicted sex offender is compressed into a single decade.

Who has Stephen Bear dated?

Stephen Bear has been linked to several prominent reality TV personalities over the past decade. His romantic history is a roll call of British reality television, with each relationship carrying its own public controversy.

Vicky Pattison

Bear dated Vicky Pattison, the former Geordie Shore star, from 2014 to 2016. Their relationship played out on social media and in the tabloids, with Pattison later publicly calling Bear “vile” and “conniving” according to reports (IMDb News). The couple lived together for a period before separating.

Charlotte Crosby

In 2018, Bear was in a relationship with Charlotte Crosby, another Geordie Shore star. Crosby has spoken negatively about Bear in subsequent media interviews. The exact timeline of their relationship remains unconfirmed, but it was brief and public.

Jessica Smith

Bear was engaged to Jessica Smith in 2017. The engagement was publicised on Instagram, where Smith later shared her personal response to the relationship’s end. The engagement did not lead to marriage.

Georgia Harrison

Bear’s relationship with Georgia Harrison, a former Love Island contestant, is the most consequential, because it directly led to his criminal conviction. The recorded encounter at issue took place in Bear’s garden in Loughton, Essex (IMDb News). Harrison later waived her right to anonymity in the criminal case (Crown Prosecution Service).

Did Vicky Pattison date Stephen Bear?

Yes. Vicky Pattison and Stephen Bear were in a relationship from 2014 to 2016. It is one of the most documented of his early relationships, with both appearing together at events and on social media.

Length and context of their relationship

• They met through the reality TV circuit.
• The relationship lasted approximately two years.
• They lived together at one point.

Vicky Pattison’s public statements about Stephen Bear

Following their split, Pattison became one of Bear’s most vocal critics. She has described him in interviews as “vile” and “conniving” (IMDb News). Pattison has also discussed the emotional impact of their relationship publicly.

The implication: Pattison’s willingness to speak out made her one of the first public figures to frame Bear’s behaviour as a pattern, not an isolated incident.

Who is Stephen Bear’s ex-fiancée?

Bear has been engaged twice — first to Jessica Smith in 2017, and later to Taylor Fisher in 2019.

Jessica Smith engagement

Bear proposed to Jessica Smith in 2017. The engagement was shared on Instagram. Smith has since taken to social media to share her perspective on their relationship, describing her personal response to the breakup.

Taylor Fisher engagement

In 2019, Bear was engaged to Taylor Fisher. This relationship received less public attention than his prior engagement but confirmed a pattern of rapid, public proposals.

What diagnosis does Vicky Pattison have?

Vicky Pattison has spoken publicly about her health, but specific details of any clinical diagnosis are not confirmed in the available inputs. She has been open about mental health challenges, including anxiety and the emotional toll of her relationship with Bear (IMDb News).

The catch: Without confirmed medical documentation from Pattison herself or official records, any specific diagnosis remains in the realm of personal disclosure rather than verified fact.

Did Charlotte Crosby date Stephen Bear?

Yes. Charlotte Crosby and Stephen Bear were in a relationship in 2018.

Relationship timeline

• They dated for a brief period in 2018.
• Neither party has confirmed exact start or end dates.

Public aftermath

Crosby has spoken negatively about Bear in media interviews since the split. Her comments align with the broader pattern of his ex-partners expressing regret or criticism about the relationship.

What this means: Crosby’s experience repeats the template — a short, public relationship followed by negative commentary — suggesting a consistent pattern in Bear’s approach to relationships.

Was Vicky Pattison with Stephen Bear?

Yes. Vicky Pattison and Stephen Bear were in a confirmed relationship from 2014 to 2016. This is the most documented of his early relationships, with multiple public appearances and reported living arrangements (IMDb News).

The trade-off: For Pattison, the relationship brought increased media attention early in her career but later became a source of public trauma she has since spoken about extensively.

How old is Jessica Lily?

The exact age of Jessica Lily — who has been linked to Bear in recent reporting — is not publicly confirmed from available sources. Her age and relationship details remain unclear.

The legal case: What Stephen Bear was convicted of

Stephen Bear’s conviction is the defining event of his public life. The legal case that sent him to prison involved recording and sharing sexual activity without consent.

The facts, verified by multiple official sources:

• December 2022: Bear was found guilty at Chelmsford Crown Court of voyeurism and two counts of disclosing private sexual photographs and films with intent to cause distress (Crown Prosecution Service).
• The jury found him guilty of two counts by unanimous verdict and one count of voyeurism by a majority verdict of 10 to 2 (Goodto).
• 3 March 2023: Sentenced to 21 months in prison (The Guardian).
• The court also required Bear to register as a sex offender and prohibited him from contacting Harrison for five years (The Guardian).
• 26 July 2023: A civil court ordered Bear to pay Harrison £207,900 in damages and imposed an injunction preventing further disclosure (Hamlins LLP).
• March 2024: Bear was ordered to pay £22,305 under the Proceeds of Crime Act from profits made illegally sharing the sex tape (BBC News).

“The CPS was able to bring a strong case because the defendant had filmed himself and Ms Harrison on his own home CCTV system — which he then distributed, sold and shared over the internet.”

— Crown Prosecution Service (East of England), commenting on the case

The pattern: Bear’s case became a landmark for image-based abuse prosecutions because it combined a celebrity perpetrator, a victim willing to waive anonymity, and clear CCTV evidence that left the defence with no credible alternative narrative.

Timeline: Stephen Bear’s life and relationships

Ten key dates that chart Bear’s journey from reality TV winner to convicted sex offender:

• 15 January 1990 — Stephen Henry Bear born in Loughton, Essex.
• August 2016 — Wins Celebrity Big Brother 18.
• 2014–2016 — Relationship with Vicky Pattison.
• 2017 — Engaged to Jessica Smith.
• 2018 — Relationship with Charlotte Crosby.
• 20 May 2020 — Arrested on suspicion of actual bodily harm on his girlfriend.
• December 2022 — Found guilty at trial at Chelmsford Crown Court.
• March 2023 — Jailed for 21 months for voyeurism and disclosing private sexual photographs.
• July 2023 — Ordered to pay £207,900 in civil damages to Georgia Harrison.
• Current — Pursuing professional boxing career; reportedly released from prison early 2024.

Confirmed facts vs. what remains unclear

Separating verified information from speculation is essential with a story that has attracted intense tabloid coverage:

Confirmed facts

• Stephen Bear was convicted in 2023 for voyeurism and disclosing private sexual photographs (Crown Prosecution Service).
• He dated Vicky Pattison from 2014 to 2016.
• He was engaged to Jessica Smith in 2017.
• He won Celebrity Big Brother 18 (IMDb News).
• He is active on Instagram as @stephenbearr.

What remains unclear

• Exact age of Jessica Lily.
• Specific diagnosis details for Vicky Pattison’s health condition.
• Exact dates of the Charlotte Crosby relationship.

What’s next for Stephen Bear?

Bear’s post-prison life revolves around his stated ambition to become a professional boxer. He has publicly claimed he wants to become the first reality star to turn professional and win the undisputed heavyweight title. As of the latest available reporting, no professional fight has been confirmed.

His civil obligations remain active: the injunction prohibiting him from publishing or disclosing the videos of Georgia Harrison continues, and the Proceeds of Crime Act order requires him to pay £22,305 in illicit gains (BBC News).

“Bear’s case demonstrates that the CPS will prosecute perpetrators of image-based abuse — even when the perpetrator is a celebrity figure. The law applies equally to everyone.”

— Crown Prosecution Service (East of England), public statement

For Stephen Bear, the choice is clear: a professional boxing career requires a licence from a body that must consider criminal convictions and sex offender registration, or he returns to the reality TV world that made him — but with a record that most production companies cannot ignore.

For a detailed breakdown of his romantic history, including key partners and milestones, check out Stephen Bears relationship timeline.

Frequently asked questions